Discovery of multi-target receptor tyrosine kinase inhibitors as novel anti-angiogenesis agents
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1 Discovery of multi-target receptor tyrosine kinase inhibitors as novel anti-angiogenesis agents Jinfeng Wang, Lin Zhang, Xiaoyan Pan, Bingling Dai, Ying Sun, Chuansheng Li, Jie Zhang School of Pharmacy, Health Science Center, Xi'an Jiaotong University, No. 76, Yanta West Road, Xi an, , P.R. China Table of Contents 1. The nomenclature, structure, melting point, HRMS, 1 H-NMR spectra, 13 C-NMR spectra of Title Compounds (CDAU-1~CDAU-11). 2. The nomenclature, structure, melting point, HRMS, 1 H-NMR spectra, 13 C-NMR spectra of Title Compounds (CDAU-12~CDAU-25). Corresponding author. Tel/Fax: ; zhj8623@xjtu.edu.cn (Jie Zhang).
2 N-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecar boxamide(cdau-1) m/z
3 mp:270~272, HRMS m/z calcd for C 23 H 19 F 3 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.21 (s, 1H), 8.99 (s, 1H), 8.63 (d, J = 2.2 Hz, 1H), 8.14 (d, J = 8.7 Hz, 2H), 8.04 (m, J = 8.7, 2.4 Hz, 1H), 7.65 (t, J = 8.3 Hz, 4H), 7.58 (d, J = 8.7 Hz, 2H), 2.03 (t, J = 12.3, 8.6, 4.8 Hz, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , , , , 14.69, N-(5-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarb oxamide(cdau-2) m/z
4 mp:273~275, HRMS m/z calcd for C 23 H 18 ClF 3 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.10 (s, 1H), 8.95 (s, 1H), 8.63 (d, J = 2.4 Hz, 1H), 8.14 (d, J = 8.7 Hz, 1H), (m, 1H), 8.04 (s, 1H), 7.67 (d, J = 8.7 Hz, 2H), (m, 2H), 7.53 (t, J = 7.9 Hz, 1H), 7.33 (d, J = 7.6 Hz, 1H), 2.03 (m, J = 12.1, 8.5, 4.7 Hz, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , , , , 14.70, 8.14.
5 N-(5-(4-(3-(3,4-bis(trifluoromethyl)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxa mide(cdau-3) m/z
6 mp:241~243, HRMS m/z calcd for C 24 H 18 F 6 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.44 (s, 1H), 9.14 (s, 1H), 8.63 (d, J = 2.1 Hz, 1H), 8.15 (d, J = 8.9 Hz, 3H), 8.05 (m, J = 8.7, 2.4 Hz, 1H), 7.67 (t, J = 5.9 Hz, 3H), 7.60 (d, J = 8.7 Hz, 2H), (m, 1H), 0.82 (m, J = 14.6, 6.4 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , , , , 14.68, N-(5-(4-(3-(3,4-difluorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU -4) m/z
7 mp:280~282, HRMS m/z calcd for C 22 H 18 F 2 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.94 (s, 1H), 8.89 (s, 1H), 8.62 (d, J = 2.1 Hz, 1H), 8.14 (d, J = 8.7 Hz, 1H), 8.04 (m, J = 8.7, 2.3 Hz, 1H), (m, 2H), 7.56 (d, J = 8.6 Hz, 2H), 7.35 (m, J = 19.6, 9.3 Hz, 1H), 7.14 (d, J = 9.0 Hz, 1H), (m, 1H), 0.82 (m, J = 14.9, 6.4 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , ,
8 135.90, , , , , , , , , , , , , , 14.71, N-(5-(4-(3-(3-chloro-4-methylphenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide( CDAU-5) Inten. (x100,000) m/z
9 mp:229~231, HRMS m/z calcd for C 23 H 21 ClN 4 O 2 ([M+2H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 2H), 8.91 (s, 1H), 8.85 (s, 1H), 7.71 (m, J = 5.3, 3.3 Hz, 3H), 7.59 (d, J = 8.7 Hz, 2H), 7.22 (m, J = 8.3, 5.1 Hz, 2H), 2.27 (s, 3H), (m, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , 19.29, 14.80, N-(5-(4-(3-(3-chlorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide (CDAU-6) m/z
10 mp:270~272, HRMS m/z calcd for C 22 H 19 ClN 4 O 2 ([M+2H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 4H), 7.72 (d, J = 8.2 Hz, 3H), 7.60 (d, J = 8.2 Hz, 2H), 7.31 (d, J = 6.2 Hz, 2H), 7.04 (d, J = 6.0 Hz, 1H), 2.18 (s, 1H), 0.85 (s, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , 14.79, 8.47.
11 N-(5-(4-(3-(2-fluorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide (CDAU-7) m/z
12 mp:222~224, HRMS m/z calcd for C 22 H 19 FN 4 O 2 ([M+2H] + ) , found m/z = H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.26 (s, 1H), 8.96 (s, 2H), 8.62 (d, J = 2.2 Hz, 1H), 8.17 (d, J = 1.3 Hz, 1H), 7.73 (d, J = 8.7 Hz, 2H), 7.60 (d, J = 8.7 Hz, 2H), (m, 1H), 7.15 (d, J = 7.6 Hz, 1H), 7.03 (d, J = 7.0 Hz, 1H), 2.16 (s, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , , 14.79, N-(5-(4-(3-(4-(trifluoromethoxy)phenyl)ureido)phenyl)cyclopropanecarboxamide (CDAU-8) m/z
13 mp:236~238, HRMS m/z calcd for C 23 H 19 F 3 N 4 O 3 ([M+2H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 3H), 8.93 (s, 1H), 7.72 (d, J = 8.7 Hz, 2H), (m, 4H), 7.31 (d, J = 8.6 Hz, 2H), (m, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , 14.79, 8.47.
14 N-(5-(4-(3-(tert-butyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU-9) m/z
15 mp:214~216, HRMS m/z calcd for C 20 H 24 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.92 (s, 2H), 8.42 (s, 1H), 7.63 (d, J = 8.6 Hz, 2H), 7.49 (d, J = 8.6 Hz, 2H), 6.04 (s, 1H), 2.17 (s, 1H), 1.31 (s, 9H), 0.83 (d, J = 7.9 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , 49.94, 29.46, 14.76, N-(5-(4-(3-(2-(dimethylamino)ethyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(C DAU-10) O H N O H N N N H N m/z
16 mp:214~216, HRMS m/z calcd for C 20 H 25 N 5 O 2 ([M+2H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.93 (s, 2H), 8.87 (s, 1H), 7.65 (d, J = 8.6 Hz, 2H), 7.52 (d, J = 8.6 Hz, 2H), 6.18 (s, 1H), 3.19 (d, J = 5.6 Hz, 2H), 2.32 (m, J = 11.0, 4.8 Hz, 2H), 2.17 (s, 7H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , 58.93, 45.51, 37.41, 14.77, 8.45.
17 N-(4-(6-(cycloropanecarboxamido)pyridin-3-yl)phenyl)-2,2-dimethylhydrazinecarboxamide( CDAU-11) m/z
18 mp:230~232, HRMS m/z calcd for C 18 H 20 N 4 O 2 ([M+2H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.94 (s, 2H), 8.45 (s, 1H), 7.64 (q, J = 8.9 Hz, 4H), 2.95 (s, 6H), (m, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , 36.72, 14.77, N-(6-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarb oxamide(cdau-12) m/z
19 mp:207~209, HRMS m/z calcd for C 23 H 18 ClF 3 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.23 (s, 1H), 9.05 (s, 1H), 8.15 (d, J = 2.2 Hz, 1H), 8.04 (d, J = 8.8 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.65 (d, J = 3.2 Hz, 2H), 7.61 (d, J = 5.4 Hz, 2H), 7.59 (d, J = 4.1 Hz, 1H), 2.09 (m, J = 7.4, 5.1 Hz, 1H), 0.83 (m, J = 9.0, 3.2 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , ,
20 139.73, , , , , , , , , , , , 25.42, 14.68, N-(6-(4-(3-(4-chloro-3-methylphenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide( CDAU-13) m/z
21 mp:272~274, HRMS m/z calcd for C 23 H 21 ClN 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.91 (s, 1H), 8.84 (s, 1H), 8.03 (d, J = 8.7 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.73 (d, J = 1.9 Hz, 1H), 7.60 (d, J = 1.2 Hz, 2H), 7.58 (s, 1H), 7.26 (d, J = 8.4 Hz, 1H), 7.21 (m, J = 8.3, 2.0 Hz, 1H), 2.27 (s, 3H), (m, 1H), 0.83 (m, J = 14.6, 6.4 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , 19.29, 14.68, N-(6-(4-(3-(4-fluorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU-14) m/z
22 mp:278~280, HRMS m/z calcd for C 22 H 19 FN 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.87 (s, 1H), 8.77 (s, 1H), 8.03 (d, J = 8.8 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.59 (d, J = 2.7 Hz, 2H), 7.57 (d, J = 1.5 Hz, 1H), (m, 2H), (m, 2H), 2.10 (m, J = 7.5, 5.0 Hz, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , 14.69, 8.10.
23 N-(6-(4-(3-(4-(tert-butyl)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDA U-15) m/z
24 mp:209~211, HRMS m/z calcd for C 26 H 28 N 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.82 (s, 1H), 8.65 (s, 1H), 8.03 (d, J = 8.7 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.79 (t, J = 7.9 Hz, 1H), 7.59 (d, J = 7.0 Hz, 2H), 7.57 (d, J = 5.8 Hz, 1H), 7.40 (d, J = 8.7 Hz, 2H), 7.31 (d, J = 8.7 Hz, 2H), (m, 1H), 1.27 (s, 9H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , 34.36, 31.72, 14.69, N-(6-(4-(3-(2-chlorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU-16 ) m/z
25 mp:276~278, HRMS m/z calcd for C 22 H 19 ClN 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.61 (s, 1H), 8.38 (s, 1H), 8.19 (m, J = 8.3, 1.4 Hz, 1H), 8.05 (d, J = 8.7 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.61 (d, J = 6.5 Hz, 2H), 7.59 (d, J = 5.0 Hz, 1H), 7.48 (m, J = 8.0, 1.4 Hz, 1H), (m, 1H), 7.05 (td, J = 7.9, 1.5 Hz, 1H), 2.10 (dq, J = 7.6, 5.0 Hz, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ
26 173.16, , , , , , , , , , , , , , , , , 14.69, N-(6-(4-(3-(3-isopropylphenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU- 17) m/z
27 mp:207~209, HRMS m/z calcd for C 25 H 26 N 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.84 (s, 1H), 8.69 (s, 1H), 8.03 (d, J = 8.7 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.79 (t, J = 7.9 Hz, 1H), 7.60 (d, J = 8.5 Hz, 2H), 7.58 (d, J = 6.8 Hz, 1H), 7.39 (s, 1H), 7.28 (d, J = 8.1 Hz, 1H), 7.21 (t, J = 7.8 Hz, 1H), 6.88 (d, J = 7.5 Hz, 1H), (m, 1H), (m, 1H), 1.22 (s, 3H), 1.20 (s, 3H), 0.84 (m, J = 8.5, 6.5 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , 140, , , , , , , , , , , 33.98, 24.34, 14.69, N-(6-(4-(3-(3-chlorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU-18 ) m/z
28 mp:216~218, HRMS m/z calcd for C 22 H 19 ClN 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 2H), 8.04 (d, J = 8.7 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.76 (d, J = 1.8 Hz, 1H), 7.60 (d, J = 5.0 Hz, 2H), 7.58 (d, J = 3.5 Hz, 1H), (m, 1H), (m, 1H), 7.04 (m, J = 7.3, 1.8 Hz, 1H), (m, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , ,
29 140.90, , , , , , , , , , , , 14.69, N-(6-(4-(3-(4-(trifluoromethoxy)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamid e(cdau-19) m/z
30 mp:276~278, HRMS m/z calcd for C 23 H 19 F 3 N 4 O 3 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 1H), 8.93 (s, 1H), 8.04 (d, J = 8.7 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.61 (d, J = 1.8 Hz, 2H), 7.59 (d, J = 4.7 Hz, 2H), 7.58 (d, J = 3.9 Hz, 1H), 7.31 (d, J = 8.6 Hz, 2H), (m, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , 14.68, N-(6-(4-(3-(2,4-dichlorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU -20) m/z
31 mp:222~224, HRMS m/z calcd for C 22 H 18 Cl 2 N 4 O 2 ([M] + ) 44807, found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.64 (s, 1H), 8.46 (s, 1H), 8.23 (d, J = 8.9 Hz, 1H), 8.06 (d, J = 8.5 Hz, 2H), 7.98 (d, J = 8.1 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.64 (d, J = 2.2 Hz, 1H), 7.61 (s, 2H), 7.59 (s, 1H), (m, 1H), 2.09 (s, 1H), 0.83 (d, J = 7.7 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , 14.69, 8.10.
32 N-(6-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide( CDAU-21) m/z
33 mp:275~277, HRMS m/z calcd for C 23 H 19 F 3 N 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.12 (s, 1H), 9.00 (s, 1H), 8.07 (s, 1H), 8.05 (d, J = 8.8 Hz, 2H), 7.99 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 7.9 Hz, 1H), 7.62 (d, J = 8.7 Hz, 2H), 7.59 (d, J = 7.6 Hz, 2H), 7.53 (t, J = 7.9 Hz, 1H), 7.33 (d, J = 7.5 Hz, 1H), (m, 1H), 0.83 (m, J = 16.0, 4.7 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , , 14.68, N-(6-(4-(3-(2,4-difluorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU -22) m/z
34 mp:273~275, HRMS m/z calcd for C 22 H 18 F 2 N 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 1H), 8.94 (s, 1H), 8.04 (d, J = 8.8 Hz, 2H), 7.98 (d, J = 8.2 Hz, 1H), 7.80 (t, J = 8.0 Hz, 1H), 7.70 (md, J = 13.4, 7.4, 2.6 Hz, 1H), 7.60 (d, J = 2.1 Hz, 2H), 7.58 (s, 1H), 7.36 (m, J = 19.7, 9.2 Hz, 1H), (m, 1H), 2.10 (m, J = 7.5, 5.0 Hz, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , ,
35 140.89, , , , , , , , , , , , , 14.68, N-(6-(4-(3-(2-fluorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU-23) m/z
36 mp:239~241, HRMS m/z calcd for C 22 H 19 FN 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 9.27 (s, 1H), 8.63 (s, 1H), 8.18 (t, J = 7.9 Hz, 1H), 8.05 (d, J = 8.4 Hz, 2H), 7.98 (d, J = 8.0 Hz, 1H), 7.80 (t, J = 7.8 Hz, 1H), 7.60 (d, J = 3.8 Hz, 2H), 7.59 (s, 1H), (m, 1H), 7.16 (t, J = 7.5 Hz, 1H), 7.03 (d, J = 5.5 Hz, 1H), 2.10 (s, 1H), 0.83 (d, J = 8.0 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , 14.69, N-(6-(4-(3-(3-fluorophenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDAU-24) m/z
37 mp:275~277, HRMS m/z calcd for C 22 H 19 FN 4 O 2 ([M+H] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.99 (s, 1H), 8.95 (s, 1H), 8.04 (d, J = 8.7 Hz, 2H), 7.99 (d, J = 8.2 Hz, 1H), 7.79 (t, J = 7.9 Hz, 1H), 7.61 (d, J = 8.8 Hz, 2H), 7.58 (d, J = 7.8 Hz, 1H), 7.54 (m, J = 8.0, 6.0 Hz, 1H), 7.32 (m, J = 15.2, 8.1 Hz, 1H), (m, 1H), 6.80 (t, J = 8.4, 2.2 Hz, 1H), (m, 1H), (m, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ ,
38 164.10, , , , , , , , , , , , , , , , , , , , , 14.70, N-(6-(4-(3-(2,6-dimethylphenyl)ureido)phenyl)pyridin-2-yl)cyclopropanecarboxamide(CDA U-25) m/z
39 mp:202~204, HRMS m/z calcd for C 24 H 24 N 4 O 2 ([M] + ) , found H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.96 (s, 1H), 8.01 (d, J = 8.8 Hz, 2H), 7.97 (d, J = 8.0 Hz, 1H), 7.80 (d, J = 2.8 Hz, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.59 (d, J = 7.9 Hz, 2H), 7.57 (d, J = 6.3 Hz, 1H), (m,2h), 2.23 (s,6h), (m, 1H), 0.83 (m, J = 14.8, 6.2 Hz, 4H). 13 C NMR (101 MHz, DMSO-d 6 ) δ , , , , , , , , , , , , , , , , , 18.74, 14.68, 8.09.
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